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Chemical Structure| 104901-43-1
Chemical Structure| 104901-43-1
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Product Details of [ 104901-43-1 ]

CAS No. :104901-43-1 MDL No. :MFCD00144769
Formula : C9H9BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :MASRAGFWFYHMFI-UHFFFAOYSA-N
M.W : 229.07 Pubchem ID :7015747
Synonyms :

Calculated chemistry of [ 104901-43-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.39
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.54
Log Po/w (XLOGP3) : 2.83
Log Po/w (WLOGP) : 2.54
Log Po/w (MLOGP) : 2.97
Log Po/w (SILICOS-IT) : 2.84
Consensus Log Po/w : 2.74

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.28
Solubility : 0.12 mg/ml ; 0.000523 mol/l
Class : Soluble
Log S (Ali) : -3.04
Solubility : 0.209 mg/ml ; 0.000912 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.72
Solubility : 0.0436 mg/ml ; 0.000191 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.63

Safety of [ 104901-43-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 104901-43-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 104901-43-1 ]
  • Downstream synthetic route of [ 104901-43-1 ]

[ 104901-43-1 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 124-41-4 ]
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  • [ 3556-83-0 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 19, p. 7694 - 7700
  • 2
  • [ 104901-43-1 ]
  • [ 35066-32-1 ]
YieldReaction ConditionsOperation in experiment
76.3% at 25 - 140℃; for 16 h; Inert atmosphere B2 (2.4g) and CuCN (3.0g) were added to DMF (50mL) at 25 °C under Ar. The reaction mixture was stirred at140°C for 16h. TLC (Petroleum ether: EA=10:1, Rf =0.5) showed the starting material was consumed completely. Thereaction mixture was poured into 150 mL of water and extracted with DCM (150 mL). The organic layer was washed with water (100mLx3) and brine (100 mL), dried over Na2SO4 and concentrated. The residue was purified by columnchromatography TLC to give the product B3 (1.4 g, 76.3percent).
Reference: [1] Patent: EP3388433, 2018, A1, . Location in patent: Paragraph 0191
  • 3
  • [ 104901-43-1 ]
  • [ 35066-32-1 ]
Reference: [1] Patent: US6417200, 2002, B1,
  • 4
  • [ 104901-43-1 ]
  • [ 18595-18-1 ]
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 43, p. 5625 - 5628
  • 5
  • [ 104901-43-1 ]
  • [ 90484-53-0 ]
Reference: [1] Patent: WO2013/149997, 2013, A1,
[2] Patent: WO2013/149997, 2013, A1,
[3] Patent: WO2013/149997, 2013, A1,
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 7, p. 854 - 881
[5] Patent: WO2017/2078, 2017, A1,
  • 6
  • [ 67-56-1 ]
  • [ 7697-26-9 ]
  • [ 104901-43-1 ]
YieldReaction ConditionsOperation in experiment
100% at 60℃; for 42 h; Preparation 38
Methyl-3-bromo-4-methylbenzoate
A suspension of 3-bromo-4-methylbenzoic acid (2.0 g, 9.30 mmol) in methanol (20 ml) was treated with sulfuric acid (0.04 ml) and the reaction mixture was stirred at 60° C. for 42 hours.
The reaction mixture was concentrated and the residue was taken up in ethyl acetate.
The organic solution was washed with sat'd NaHCO3(aq.), dried (MgSO4), filtered, and concentrated to give the title compound as an orange oil which was suitable for use without further purification (2.25 g, quant.).
95% at 60℃; Intermediate 15: 3-Bromo-4-(tert-butoxycarbonylamino-methyl)-benzoic acidTo a suspension of 3-Bromo-4-methylbenzoic acid (300 g, 1 .39 mol) in MeOH (3 L) was added H2S04 (6 ml). The reaction mixture was stirred at 60°C overnight. The reaction was cooled to room temperature, evaporated and the residue was dissolved in EtOAc (2 L), The EtOAc solution was washed with saturated NaHC03 (1 L), dried over MgS04 and concentrated to dryness to give the corresponding methyl ester as pale yellow oil (303 g, 95percent yield).
95% at 60℃; for 16 h; To a suspension of 3-bromo-4-methylbenzoic acid 2 (300 g, 1.39 mol) in MeOH (3 L) was added H2SO4 (6 ml). The reaction mixture was stirred at 60 °C overnight. The reaction was cooled to room temperature, evaporated and the residue was dissolved in EtOAc (2 L). The EtOAc solution was washed with saturated NaHCO3 (1 L), dried over MgSO4 and concentrated to dryness to give the corresponding methyl ester as pale yellow oil (303 g, 95percent yield).
93% at 60℃; [0343] Ex-32C: In a 500 mL round-bottom flask 3-bromo-4-methyl-benzoic acid (25.0 g, 116.3 mmol), was combined with MeOH (250 mL) and H2SO4 (0.5 mL) was added. The resulting solution was heated to 60 0C and aged overnight. The reaction was cooled to room temperature, concentrated to 1/5 the volume, diluted with EtOAc and saturated NaHCO3 and the layers were cut. The organic layer was washed with H2O, dried with MgSO4 and concentrated to dryness. The crude was purified by crystallization from EtOAc and hexanes to provide 24.8 g (93percent) of 3-bromo-4-methyl-benzoic acid methyl ester. 1H-NMR (CDCl3) δ 8.18 (d, J= 2.1 Hz, IH), 7.85 (dd, J = 8.1, 1.9 Hz, IH), 7.28 (d, J= 8.1 Hz, IH), 3.90 (s, 3H), 2.44 (s, 3H).

Reference: [1] Patent: US2013/237537, 2013, A1, . Location in patent: Paragraph 0330-0331
[2] Patent: WO2013/119946, 2013, A1, . Location in patent: Paragraph 0198; 0345
[3] Patent: WO2011/107608, 2011, A1, . Location in patent: Page/Page column 69
[4] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 23, p. 6442 - 6446
[5] Patent: WO2006/4903, 2006, A2, . Location in patent: Page/Page column 125
[6] Journal of the American Chemical Society, 2002, vol. 124, # 50, p. 14993 - 15000
[7] Patent: US2013/237538, 2013, A1, . Location in patent: Paragraph 0346
[8] Patent: WO2017/195069, 2017, A1, . Location in patent: Paragraph 34
[9] Patent: EP3388433, 2018, A1, . Location in patent: Paragraph 0190
  • 7
  • [ 99-75-2 ]
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Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 24 - 32[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 1, p. 30 - 39
[3] Journal of Organic Chemistry, 1988, vol. 53, # 23, p. 5545 - 5547
[4] Journal of the American Chemical Society, 1984, vol. 106, # 6, p. 1650 - 1663
[5] European Journal of Organic Chemistry, 2009, # 2, p. 223 - 237
  • 8
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YieldReaction ConditionsOperation in experiment
63% With NaH In hexane; N,N-dimethyl-formamide A
methyl 3-bromo-4-methylbenzoate
To a mixture of hexane washed 60percent disp. NaH (2.28 g, 57 mmol) in DMF (250 mL), 0° C., was added 3-bromo-4-methylbenzoic acid (10.03 g, 46.6 mmol).
After 30 min, the reaction was warmed to room temperature, diluted with EtOAc (1.25 L) and washed with H2O (5*250 mL).
The organic layer was MgSO4 dried and concentrated.
The residue was chromatographed (~375 g silica, 10percent EtOAc/CH2Cl2) to give the desired product as a solid (16.68 g, 63percent); IR(CHCl3): 1260, 1294, 1437, 1721 cm-1; NMR(300 MHz, CDCl3): 2.46 (s, 3H); 3.92 (s, 3H); 7.31 (d, 1H, J=7.8 Hz); 7.88 (d, 1H, J=7.8 Hz); 8.21 (s, 1H); MS(FD): 228.0.
Analysis for C9H9BrO2: Calculated: C, 47.19; H, 3.96. Found: C, 47.06; H, 3.92.
Reference: [1] Patent: US6417200, 2002, B1,
  • 9
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  • [ 18107-18-1 ]
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Reference: [1] Patent: EP2444402, 2012, A1, . Location in patent: Page/Page column 45
  • 10
  • [ 7697-26-9 ]
  • [ 77-78-1 ]
  • [ 104901-43-1 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 19, p. 7694 - 7700
  • 11
  • [ 99-75-2 ]
  • [ 2417-72-3 ]
  • [ 104901-43-1 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 24 - 32[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 1, p. 30 - 39
  • 12
  • [ 104901-43-1 ]
  • [ 73183-34-3 ]
  • [ 882679-40-5 ]
YieldReaction ConditionsOperation in experiment
84% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; for 16 h; Inert atmosphere Methyl 3-bromo-4-methylbenzoate (3 mL, 19.2 mmol) was dissolved in 1,4-dioxane (96 mL), and bis(pinacolato)diboron (7.31 g, 28.2 mmol), potassium acetate (5.65 g, 57.6 mmol), and Pd(dppf)Cl2 (2.8 g, 3.84 mmol) were added thereto. The resulting mixture was replaced with argon, and stirred at 90°C for 16 hours. The mixture was cooled to room temperature, and water was added. Then, the mixture was extracted with EtOAc. An organic layer was dried over magnesium sulfate, concentrated, and then purified using silica gel chromatography to obtain the title compound (off-white solid, 4.46 g, and 84percent yield). 1H NMR (300 MHz, CDCl3) δ 8.40 (d, 1H), 7.97 (dd, 1H), 7.23 (d, 1H), 3.94-3.87 (m, 3H), 2.58 (s, 3H), 1.35 (d, 12H).
Reference: [1] Chemical Communications, 2012, vol. 48, # 34, p. 4115 - 4117
[2] Patent: EP2963027, 2016, A1, . Location in patent: Paragraph 0470; 0471; 0472
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 4869 - 4881
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